Sodium Iodide → (S)-1-(Benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropane

HRID 1463780Notes

Reaction equation

HRID 1463780 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([O:17][CH2:18][P:19]([O:25][CH:26]([CH3:28])[CH3:27])([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])[CH2:11]OS(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:29].[Na+]>CC(C)=O>[CH2:1]([O:8][CH2:9][C@H:10]([O:17][CH2:18][P:19]([O:25][CH:26]([CH3:28])[CH3:27])([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])[CH2:11][I:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 22851229HCID 22851229, compound

Product 1

HCID 15667219(S)-1-(Benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropaneYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (R)-3-O-benzyl-2-O-[(diisopropylphosphono)methyl]-1-O-(methanesulfonyl)glycerol (10.0 g, 22.8 mmol) and sodium iodide (5.15 g, 34.4 mmol) in 70 mL of acetone was heated at reflux for 14 hours. The mixture was concentrated to about 30 mL volume, and insoluble material was removed by filtration. The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (methylene chloride:acetone=1:0 to 5:1) to give 9.51 g (89%) of the title compound as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 14 hours
  3. concentrationThe mixture was concentrated to about 30 mL volume, and insoluble material
  4. customwas removed by filtration
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by flash chromatography on silica gel (methylene chloride:acetone=1:0 to 5:1)

Sources & evidence

ORD record
ord-76dd8f9bd5634db5a430418d4e35c513
Source dataset
uspto-grants-1994_04
Patent number
US05302585

Reaction notes

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